19.5-Mile Rail-Trail Through Orange County, NY
Heritage Trail access at Chester, Chester, NY 10918
Research updated May 2026
Age
All Ages
Cost
Free
Free
Access
Wheelchair OK
Paved and limestone surface; mixed
Equipment
Photos OK
Est. 1830 · Built on historic Erie Railroad Main Line corridor · Passes early-1700s European settlements · Protected cemeteries along the route
The Orange Heritage Trail is a 19.5-mile rail-trail in Orange County, New York, built along the historic Erie Railroad Main Line and currently spanning approximately 11.85 miles from the Town of Monroe to Hartley Road in the Town of Goshen near Middletown. The trail features both asphalt and crushed limestone surfaces, with access points in Monroe, Chester, and Goshen. Chester was first settled by Europeans in the early 1700s, and old cemeteries are still being identified within the town; Chester has enacted the Chester Cemeteries Protection Law to safeguard graveyards and burial sites from commercial or residential development. A small cemetery (variously identified as Tuthill Cemetery or Oxford Depot Cemetery) sits along the right-hand side of the trail; other graves date to the 1600s, and some interred individuals were alive during the Revolutionary War. The trail also passes through a bird and wildlife sanctuary with meadows and streams.
Sources
Trail-user folklore associated with the Chester section of the Heritage Trail describes phenomena observed primarily after sunset, including bright lights moving along the trail, the sound of footsteps following walkers when no one is present, whistling, and dark figures observed along the route especially in the direction of Monroe. Photographs taken at trailside cemeteries are reported to contain orbs. Many of the unexplored side trails branching from the main path are part of the surrounding wildlife preserve. These accounts circulate through regional New York rail-trail folklore and are not part of Orange County's official trail communications. Visit during daylight hours.
Media Appearances
Walk, run, or bike the Chester section of the 19.5-mile Orange Heritage Trail, which follows the historic Erie Railroad Main Line through Orange County. The trail passes small old cemeteries protected by the Chester Cemeteries Protection Law.
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